A New Synthetic Route to 3-Oxo-4-amino-1,2,3-oxadiazole from the Diazeniumdiolation of Benzyl Cyanide: Stable Sydnone Iminium <i>N</i>-Oxides

Bohle, D. Scott; Perepichka, Inna

doi:10.1021/jo802343k

Cited by 16 publications

(12 citation statements)

References 17 publications

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“…The solid was removed by filtration and dried to afford the yellow or white solid oxime 1. Oximes 1a-1o, [13] 1p, [23] 1q, [5] 1r, [24] and 1s [12] were prepared according to literature methods, and their spectroscopic data are in agreement with those in the literature. [5] Yellow solid.…”

Section: Preparation Of Oximementioning

confidence: 94%

Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N‐Aryloxindole Nitrones

Chen

Liang

et al. 2017

Eur J Org Chem

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A variety of (E)‐N‐aryloxindole nitrones were prepared in good to excellent yields by using a copper‐catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)‐oxindole nitrones. This method to prepare (E)‐N‐aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone‐derived oxindole nitrone in high yield.

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Section: Preparation Of Oximementioning

confidence: 94%

Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N‐Aryloxindole Nitrones

Chen

Liang

et al. 2017

Eur J Org Chem

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“…Details of the instrumentation used in this research are described in a recent paper. [38] The NMR spectra were measured on Varian Mercury Spectrometers with either 300, 400 or 500 MHz fields for 1 H. Chemical shifts are reported as d in ppm. Elemental analyses were performed by The Elemental Analysis Laboratory at University of Montreal.…”

Section: General Methodsmentioning

confidence: 99%

Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

et al. 2012

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By careful choice of reaction conditions 1‐methylnaphtho[1,8‐de]‐1,2,3‐triazine and 1,3‐dimethylnaphtho[1,8‐de]‐1,2,3‐triazinium triflate are readily prepared by the alkylation of 1H‐naphtho[1,8‐de]‐1,2,3‐triazine. The electronic spectra for these bathochromically shifted dyes are reported for a range of solvents as are their vibrational spectra and theoretical structures from density functional theory, B3LYP/6‐311++G**. The 15N substitution into the middle nitrogen atom allows for the identification of strong azine bands in the IR and Raman spectra as well as in the 15N NMR spectrum. X‐ray crystallography is used to characterize the solid‐state structures of two of these new triazine derivatives and these structures are used to benchmark the theoretical and spectroscopic discussions. The corresponding 1,3‐dimethyltriazinium radical is prepared and characterized by cyclic voltammetry, spectroelectrochemistry, and EPR spectroscopy. Unlike the related transient 1,2,4‐triazene radicals, the 1,3‐dimethyl‐1,2,3‐naphthotriazyl radical is markedly more stable.

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“…The actual N-N-O linkage was reported solely in five-membered rings, i.e. 1,2,3-oxadiazole derivatives [1, 5, 6]. The existence of a closed 1,2,3-oxadiazole ring was initially reported to be improbable since an open ring form is more stable, as predicted by quantum chemical modelling [29].…”

Section: Discussionmentioning

confidence: 99%

“…Much larger variability of oxadiazine and oxadiazole containing structures was generated via organic synthesis; mostly with 1,2,4 or 1,3,4 arrangement containing either O-N-C-N or O-C-N-N linkage, respectively [1, 4]. Up to date there is no report on natural metabolite containing a direct N-N-O linkage in the heterocycle (1,2,3-oxadiazine or 1,2,3-oxadiazole), although compounds containing 1,2,3-oxadiazole were synthetized via organic synthesis [5–7]. Majority of above mentioned structures exhibit interesting bioactivities including potential anticancer activity [2–4, 8].…”

Section: Introductionmentioning

confidence: 99%

The cyanobacterial metabolite nocuolin a is a natural oxadiazine that triggers apoptosis in human cancer cells

Voráčová¹,

Hájek²,

Mareš³

et al. 2017

PLoS ONE

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Oxadiazines are heterocyclic compounds containing N-N-O or N-N-C-O system within a six membered ring. These structures have been up to now exclusively prepared via organic synthesis. Here, we report the discovery of a natural oxadiazine nocuolin A (NoA) that has a unique structure based on 1,2,3-oxadiazine. We have identified this compound in three independent cyanobacterial strains of genera Nostoc, Nodularia, and Anabaena and recognized the putative gene clusters for NoA biosynthesis in their genomes. Its structure was characterized using a combination of NMR, HRMS and FTIR methods. The compound was first isolated as a positive hit during screening for apoptotic inducers in crude cyanobacterial extracts. We demonstrated that NoA-induced cell death has attributes of caspase-dependent apoptosis. Moreover, NoA exhibits a potent anti-proliferative activity (0.7–4.5 μM) against several human cancer lines, with p53-mutated cell lines being even more sensitive. Since cancers bearing p53 mutations are resistant to several conventional anti-cancer drugs, NoA may offer a new scaffold for the development of drugs that have the potential to target tumor cells independent of their p53 status. As no analogous type of compound was previously described in the nature, NoA establishes a novel class of bioactive secondary metabolites.

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A New Synthetic Route to 3-Oxo-4-amino-1,2,3-oxadiazole from the Diazeniumdiolation of Benzyl Cyanide: Stable Sydnone Iminium N-Oxides

Cited by 16 publications

References 17 publications

Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N‐Aryloxindole Nitrones

Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N‐Aryloxindole Nitrones

Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

The cyanobacterial metabolite nocuolin a is a natural oxadiazine that triggers apoptosis in human cancer cells

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